Rigorous Biogenetic Network for a Group of Indole Alkaloids Derived from Strictosidine 英文参考文献.docVIP

Molecules 2008, 13, 1875-1896; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Review Rigorous Biogenetic Network for a Group of Indole Alkaloids Derived from Strictosidine? László F. Szabó Department of Organic Chemistry, Semmelweis University, H?gyes utca 7, H-1092 Budapest, Hungary; E-mail: szalasz@szerves.sote.hu ? Chemotaxonomy of Indole Alkaloids, Part 5 (for Part 4, see [15]). This paper is dedicated to Prof. Heinz G. O. Becker on the occasion of his 85th birthday. Received: 5 August 2008; in revised form: 24 August 2008 / Accepted: 26 August 2008 / Published: 27 August 2008 Abstract: Strictosidine, the precursor of more than 2,500 indole alkaloids, was isolated from four species of three plant families. By searching the Dictionary of Natural Products on DVD it was found that about 150 indole alkaloids were obtained from the same species (coalkaloids), which is a direct proof of their common origin. On the base of their three- dimensional structure, taxonomic properties and standard reaction mechanisms an extended network was established which involved the four fundamental skeletons, the three types of carbon framework in the secologanin subunit and all major groups of indole alkaloids derived from secologanin and tryptamine (except a few minor groups, in which only less then 10 alkaloids were known). The system was extended to the heterodimer indole alkaloids and the quinoindole alkaloids as well. Keywords: Secologanin, coalkaloid, dimer alkaloid, reaction mechanism, computer searching, chemotaxonomy. Introduction The monoterpenoid indole alkaloids form a uniform group of natural products. Several generations of researchers have worked on their isolation, structure determination, chemical transformations and synthesis. Much effort has also gone into elucidating their biogenesis, and as a consequence, the main  Molecules 2008, 13 1876 pathways of